Patent GB-956007-A (GB)
Title: Stable poly-1,2-alkylene oxaglycol carbamates and derivatives thereof
IPC: C08G73/04
Filed: 1960-11-03
Abstract: The invention comprises poly-1, 2-alkylene oxaglycol carbamates of the general formula: <FORM:0956007/C2/1> wherein R1 represents hydrogen or a C1-4 alkyl group, R represents an n-valent organic radical having at least one ether oxygen linkage and n is an integer of from 2 to 4, and solutions of such compounds in an organic solvent, e.g. chloroform, benzene, trichlorethylene, toluene and diethyl ether.  R preferably represents a divalent oxa-containing aliphatic, aromatic or mixed aliphatic-aromatic radical, e.g. a radical derived from a dialkylene glycol, from a polyalkylene glycol having a molecular weight of up to 4,000, or from 4, 41-dihydroxy-diphenyl ether. Compounds of the above formula in which n is 2 and R represents an oxaglycol residue are prepared by adding 2 moles of a 1, 2-alkyleneimine having not more than 10 carbon atoms to 1 mole of a polyalkylene oxaglycol bis-chlorocarbonate. Other compounds of the above general formula are prepared analogously.  The reaction is preferably conducted in the presence of an ammonium or alkali metal carbonate or bicarbonate.  The above products may be homopolymerized or copolymerized.  Specification 956,006 is referred to.ALSO:Poly-1,2-alkylene oxaglycol carbamates of the general formula: <FORM:0956007/C3/1> wherein R represents hydrogen or a C1- 4 alkyl group, n is an integer of from 2 to 4 and R represents an n-valent organic radical having at least one ether oxygen linkage (e.g. a radical derived from a polyalkylene glycol having a molecular weight of up to 4,000), are prepared by reacting a 1,2-alkyleneimine having not more than 10 carbon atoms with a stoichiometric amount of an appropriate bis-, tris- or tetrakis-chlorocarbonate. The polyalkylene glycol radicals R include polyethylene, propylene and butylene glycols.  The above compounds may be polymerized alone or with one or more organic compounds containing at least two active hydrogen atoms per molecule, e.g. castor oils, sugars, glycols, triols, phenols, aniline, metaxylene diamine, piperazine, diethylene triamine, triethylene tetramine, tetraethyleneglycol, Emery dimerized and trimerized acids, hexamethylene dimercaptan, hydroquinone, polyesters and hide glue.  Polymerization may be effected by heating or by the use of acidic or basic promoters or an active hydrogen containing compound, e.g. zinc chloride, lead chloride, hydrochloric acid, sulphuric acid, phosphoric acid, para.-toluene sulphonic acid, boron trifluoride and its addition product with ethylamine, ethylene diamine, monoethanolamine, isophthaloylhydrazide and water.  Uses and properties: The above polymers may be used as plastics in the form of gaskets, O-rings, tubing, wire insulation, protective films and encapsulating material for electronic circuits, and also as adhesives and coatings for fabric, paper, ceramics, plastics, metals and glass. The homopolymers vary from soft rubbery polymers to flexible leathery polymers.  The above monomers may be employed as crosslinking agents for linear thermoplastic and elastomeric polymers to produce a three-dimensional polymer network.  The above monomers can be used to creaseproof fabrics sold for "wash and wear" use and to impart repellency to water and alcohol without loss of drape or hand.  Such monomers may also be used to impregnate or saturate porous substrates, such as paper, for use as filter paper, stationery and packaging wrap.  Specification 956,006 is referred to.ALSO:The resistance of hide glue to water is increased by the addition of a poly-1,2-alkylene oxoglycol carbamate of the formula: <FORM:0956007/B1-B2/1> wherein R1 represents hydrogen or a C1-4 alkyl radical, R represents an n-valent organic radical having at least one ether oxygen linkage and n is an integer of from 2 to 4. Polymers of the above carbamate monomers may also be employed as adhesives and coatings for fabric, paper, ceramics, plastics, glass and metals, as well as for the encapsulation of electronic circuits, and as insulation for wire.  Specificanion 956,006 is referred to.ALSO:A fabric composed of a polyester derived from dimethyl terephthalate and ethylene glycol is rendered water and alcohol repellent and is improved in respect of drape and bond properties; paper intended for use as filter paper, stationary and packaging wrap is improved in respect of "feel" flexibility and strength; and a high cellulose paper is rendered water and alcohol repellent by treating such materials with poly-1, 2-alkylene oxaglycol carbamates of the formula:-  <FORM:0956007/D1-D2/1> wherein R1 represents hydrogen or a C1-4 alkyl radical, R represents an n-valent organic radical having at least one ether oxygen linkage and n is an integer of from 2 to 4, followed by subsequent curing by heating.  Specification 956,006 is referred to.